It’s midnight.
I step gingerly across the floorboard. It moans with each step.
An owl hoots outside, sending shivers across my skin.
I can feel the danger. Thick.
The monster strikes from the doorway.
I scream.
Then laugh.
Halloween and Fear
It’s Halloween today.
The time of year where we welcome fear – FOR FUN!
We even pay for it, walking through “haunted” houses just to feel our hearts race.
We scream, then laugh.
It’s fun because it’s safe.
Outside Halloween, fear feels different.
It’s not fun anymore.
Because in real life, fear has consequences.
Practice Is Safe
Without consequences, things simply aren’t as scary.
Take practice.
I’ve been working on improving my tennis backhand.
In practice, it feels smooth. Controlled. Confident.
Then I play a match and I avoid it at all costs.
All that confidence disappears.
I tense up, revert to my old (bad) habits, and won’t even attempt what I felt so confident about in practice.
Because in practice, there’s no consequence.
In a match, there is.
Missing a shot costs a point. Losing a point might cost a game.
And losing feels like failure.
So even though I know the new backhand will make me better, fear tells me to stick with what’s familiar.
“Better to survive than risk looking foolish,” they say.
Or is it?
Fear Isn’t Always the Enemy
That’s how fear works.
It confuses different with dangerous.
It convinces us that safety equals success.
But most of what we fear isn’t life-threatening.
It’s ego-threatening.
It’s the discomfort of being seen while we learn.
Yet, the goal isn’t to erase fear. It’s to move through it.
For me, that means taking the new backhand into real matches, missing a few, and trusting that every miss is progress.
Fear doesn’t mean stop.
It means pay attention.
Starting Something Scary
That same feeling shows up again for me now, but off the tennis court.
Starting a business is its own kind of match.
I was telling a good friend recently:
When you start a company, no one hires you and hands you a paycheck.
You have to go find it.
There’s no fallback plan.
The consequences are real.
And yet… it’s fun.
It’s invigorating.
It’s stepping into uncertainty and trusting the swing.
Fear is still there.
But so is excitement.
They live right next to each other.
Getting Comfortable with the Uncomfortable
Most of us are probably familiar with the above phrase.
Growth doesn’t happen in comfort. Comfort keeps us safe, but it also holds us still.
The best leaders and learners know that progress lives at the edge of what we understand.
Carol Dweck calls this the growth mindset: choosing to see challenge as proof of learning, not evidence of weakness.
Andy Grove practiced it by questioning success itself, asking, “If I were replaced, what would my successor do?”
He invited discomfort on purpose because he knew that’s where clarity lives.
How to Practice It
Getting comfortable being uncomfortable isn’t about forcing ourselves into extremes.
My experience is that people tend to believe we need to do something bold to gain comfort.
We don’t. Reckless can still be reckless.
The idea is to build incrementally. To stretch out limits, not blow past them.
Don’t like public speaking?
Start with asking questions in a group setting.
Avoiding providing someone with tough feedback?
Start with small pieces of feedback.
Struggle with delegation?
Start by handing off one low-risk task.
We build tolerance to discomfort through incremental actions.
The approach shouldn’t be to leap into fear with reckless abandon.
Rather, we need to lean into it.
Consistently.
Try This:
Consider one aspect where you know fear is holding you back.
Start leaning in with small, incremental discomfort.
I’ll use my backhand as an example.
The next match I play, I’ll commit to using my newly practiced backhand at least once.
The match after that, twice. And so on.
The result doesn’t matter. I’m focused on overcoming my discomfort.
Each step reinforces leaning into discomfort.
And, getting comfortable with that discomfort.
TL;DR
Haunted houses are fun because the fear isn’t real.
In life and work, it is.
But that’s also what makes progress meaningful.
The more we force ourselves to face real discomfort, incrementally, consciously, the more tolerant we become to that discomfort.
Happy Halloween!
